Classifications

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  • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/14—Organic compounds
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  • C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/027—Neutral salts thereof
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  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/028—Overbased salts thereof
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  • C10M2207/09—Metal enolates, i.e. keto-enol metal complexes
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
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  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
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  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
  • C10M2219/088—Neutral salts
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
  • C10M2219/089—Overbased salts
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
  • C10M2223/045—Metal containing thio derivatives
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
  • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
  • C10M2227/061—Esters derived from boron
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2010/00—Metal present as such or in compounds
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  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/02—Groups 1 or 11
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/04—Groups 2 or 12
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
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  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
  • C10N2040/251—Alcohol fueled engines
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  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
  • C10N2040/252—Diesel engines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
  • C10N2040/252—Diesel engines
  • C10N2040/253—Small diesel engines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
  • C10N2040/255—Gasoline engines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
  • C10N2040/255—Gasoline engines
  • C10N2040/28—Rotary engines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2070/00—Specific manufacturing methods for lubricant compositions
  • C10N2070/02—Concentrating of additives

Definitions

• This invention relates to oil soluble additives useful in fuel and lubricating oil compositions, and particularly to concentrates or lubricating compositions containing said additives, and methods for their manufacture and use.
• the additives are various metal salts of mono-or dicarboxylic acids which have been substituted with a high molecular weight hydrocarbon group, or metal salts of the derivatives of polyolefin mono- or dicarboxylic acids, anhydrides, or esters such as amides, imides, esters, oxazolines, etc., formed by further reaction with amine, alcohol, amino alcohols, and which may be further treated, e.g. borated.
• the high molecular weight (M n ) of the polyolefin is generally greater than about 700.
• the metal salt compatibility additives are especially useful in stabilizing (or “compatibilizing") concentrates, lubricating oil or fuel oil compositions which contain high molecular weight dispersants, high total base number (“TBN”) detergents, and various antiwear or antioxidant materials. These salts may be useful in replacing at least a portion of previously used compatibility agents, antioxidants and dispersants.
• Canadian Pat. No. 895,398 discloses reacting a mole of an unsaturated hydrocarbon group of 700 to 10,000 molecular weight with 1 to 1.5 moles of chloro-substituted maleic or fumaric acid, which material can then be further reacted with alcohol.
• U.S. Pat. No. 3,927,041 discloses reacting a mole of 300 to 3,000 molecular weight polybutene containing 5 to 200 ppm 1,3 dibromo-5,5-dialkylhydantoin as a catalyst reacted with 0.8 to 5, generally 1.05 to 1.15 moles of dicarboxylic acid or anhydride, to form materials which can be used per se, or as esters, amides, iraides, amidines, in petroleum products.
• U.S. Pat. No. 3,215,707 discloses reacting chlorine with a mixture of polyolefin up to 50,000 molecular weight, especially of 250 to 3,000 molecular weight with one or more moles of maleic anhydride depending upon whether one or more succinic anhydride radicals are to be in each polymer molecule.
• U.S. Pat. Nos. 4,113,639 and 4,116,876 disc lose an example of alkenyl succinic anhydride having a molecular weight of the alkenyl group of 1,300 and a Saponification Number of 103 (about 1.3 succinic anhydride units per hydrocarbon molecule).
• This alkenyl succinic arthydride may be reacted with polyamine and then boric acid ('639), or may be reacted with amino alcohol to form an oxazoline ('876) which is then borsted by reaction with boric acid.
• U.S. Pat. No. 4,062,786 in Example 13 shows a polyisobutenyl succinic anhydride of molecular weight of about 1,300 and a Saponification Number of about 100 (about 1.25 succinic anhydride units per alkenyl group).
• metal salts of alkenyl succinic acid are known.
• U.S. Pat. No. 3,271,310 teaches that a "metal salt of hydrocarbon-substituted succinic acid having at least 50 aliphatic carbon atoms as the hydrocarbon substituent, the metal of the metal salt being selected from the class consisting of Group I metals, Group II metals, aluminum, lead, tin, cobalt and nickel" is useful as a dual purpose additive.
• U.S. Pat. No. 4,552,677 discloses a similar material in which the preferred metal in the salt is copper and the hydrocarbon substituent contains from 8 to 35 carbon atoms.
• U.S. Pat. No. 4,234,435 discloses that certain of the salts disclosed in U.S. Pat. No. 3,271,310 are useful as dispersant/detergents and viscosity improving agents in lubricating oil compositions.
• the salts include those in which the polybutene moiety had a H n of from about 1,300 to about 0 a M w /M n ratio of between 1.5 and 4.0 and in which the ratio of the succinic moiety to the polybutene substituent is at least 1.3.
• U.S. Pat. No. 3,714,042 relates to the treatment of basic metal sulfonate complexes, sulfonatecarboxylate complexes and carboxylate complexes with high molecular weight carboxylic acids to prepare additives useful in lubricating oils and gasolines.
• the patentee teaches the ineffectiveness of preformed metal salts of high molecular weight carboxylic acids for such treatments, and exemplifies the sediment formation resulting from use of the calcium salt of polyisobutenyl succinic anhydride at low concentrations in a mineral lubricating oil.
• the present invention is directed to compositions containing an additive comprising metal salts of the product of a polyolefin of at least 700 number average molecular weight (M n ) substituted with a mono- or dicarboxylic acid producing moiety per polyolefin molecule.
• the preferred salts are copper and zinc salts.
• the material is useful per se as an additive, e.g., as a dispersant, it is particularly useful as a comparability aid in lubricating compositions containing high molecular weight dispersants, high total base number detergents, antiwear agents, and antioxidants. It has been found that these salts may also be substituted for at least some of these detergents, dispersants, and antioxidant additives.
• compositions of the invention are different from the prior art in that they are quite stable even after storage at elevated temperatures.
• Lubricating oil compositions e.g. automatic transmission fluids, heavy duty oils suitable for gasoline and diesel engines, etc.
• Universal type crankcase oils those in which the same lubricating oil compositions are used for either gasoline or diesel engines, may also be prepared.
• These lubricating oil formulations conventionally contain several different types of additives that will supply the characteristics that are required for the particular use. Among these types of additives are included viscosity index improvers, antioxidants, corrosion inhibitors, detergents, dispersants, pour point depressants, antiwear agents, etc.
• a concentrate for instance, as an "adpack" containing 10 to 80 weight percent, e.g., 20 to 80 weight percent, active ingredient in a solvent.
• the solvent may be a hydrocarbon oil, e.g., a mineral lubricating oil, or other suitable material.
• these concentrates in turn, may be diluted with 3 to 100, preferably 5 to 40, parts by weight of lubricating oil per part by weight of the additive package.
• concentrates of course, to make the handling of the various constituent materials less difficult as well as to facilitate solution of or dispersion of those materials in the final blend.
• Blending of a lubricating oil composition containing several types of additives typically causes no problems if each additive is added separately.
• the additives may interact with each other.
• high molecular weight dispersants have been found to interact with various other additives in the concentrate, particularly overbased metal detergents and antioxidants, such as copper oleate, to cause phase separation. Obviously, this may hamper pumping, blending and handling of both the concentrate and the resulting product.
• the concentrate may be further diluted to reduce the interaction effect, the dilution increases shipping, storage and handling costs. Storage of the concentrate provides a problem in that the concentrate itself may separate in to a number of phases during that storage.
• hydrocarbyl mono- and dicarboxylic acid metal salts discussed below substantially alleviate these phase separation problems. Indeed, these salts may be used as substitutes for all or part of the other dispersant and antioxidant additives included in a concentrate or lubricating oil formulation.
• compositions made according to this invention generally will contain one or more:
• compositions may also include antioxidants, friction modifiers, and the like.
• compositions of this mixture contain at least four active agents listed separately above (and which are discussed separately below) in amounts effective to provide their respective functions.
• compositions of the invention When the compositions of the invention are used in the form of lubricating oil compositions, such as automotive crankcase lubricating oil compositions, a major amount of a lubricating oil may be included in the composition.
• the composition may contain about 85 to about 99.99 weight of a lubricating oil. Preferably, about 93 to about 99.8 weight percent of the lubricating oil.
• lubricating oil is intended to include not only hydrocarbon oils derived from petroleum but also synthetic oils such as alkyl esters of dicarboxylic acids, polyglycols and alcohols, polyalphaolefins, alkyl benzenes, organic esters of phosphoric acids, polysilicone oils, etc.
• compositions of this invention are provided in the form of concentrates, with or without the other noted additives, a minor amount, e.g., up to about 50 percent by weight, of a solvent, mineral or synthetic oil may be included to enhance the handling properties of the concentrate.
• the dispersant preferred in this inventive composition is a long chain hydrocarbyl substituted mono-or dicarboxylic acid material, i.e., acid, anhydride, or ester, and includes a long chain hydrocarbon, generally a polyolefin, substituted with acrylic acid or an alpha or beta unsaturated C 4 to C 10 mono or dicarboxylic acid, such as itaconic acid, maleic acid, maleic anhydride, chloromaleic acid, dimethyl fumarate, chloromaleic anhydride, acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, etc., per mole of polyolefin.
• the dispersant contains at least about 1.05 moles (e.g., 1.05 to 1.2 moles, or higher) of the acid per mole of polyolefin.
• Preferred olefin polymers for the reaction with the unsaturated dicarboxylic acids are those polymers made up of a major molar amount of C 2 to C 10 ,e.g., C 2 to C 5 , monoolefin.
• Such olefins include ethylene, propylene, butylene, isobutylene, pentene, octene-1, styrene, etc.
• the polymers may be homopolymers such as polyisobutylene or copolymers of two or more of such olefins. These include copolymers of: ethylene and propylene; butylene and isobutylene; propylene and isobutylene; etc.
• copolymers include those in which a minor molar amount of the copolymer monomers, e.g., 1 to 10 mole percent is a C 4 to C 18 diolefin, e.g., copolymer of isobutylene and butadiene; or a copolymer of ethylene, propylene and 1,4-hexadiene; etc.
• a minor molar amount of the copolymer monomers e.g., 1 to 10 mole percent is a C 4 to C 18 diolefin, e.g., copolymer of isobutylene and butadiene; or a copolymer of ethylene, propylene and 1,4-hexadiene; etc.
• the olefin polymer may be completely saturated, for example an ethylene-propylene copolymer made by a Ziegler-Natta synthesis using hydrogen as a moderator to control molecular weight.
• the olefin polymers will usually have number average molecular weights above about 700, including number average molecular weights within the range of from about 1,500 to about 5,000 with approximately one double bond per polymer chain.
• An especially suitable starting material for a dispersant additive is polyisobutylene.
• the number average molecular weight for such polymers can be determined by several known techniques. A convenient method for such determination is by gel permeation chromatography (GPC) which additionally provides molecular weight distribution information, see W. W. Yua, J. J. Kirkland and D. D. Bly, "Modern Size Exclusion Liquid Chromatography,” John Wiley and Sons, New York, 1979.
• the olefin polymer can be first halogenated, for example, chlorinated or brominated to about 1 to 8, preferably 3 to 7 weight percent chlorine, or bromine, based on the weight of polymer, by passing the chlorine or bromine through the polyolefin at a temperature of 100° to 250°, e.g., 120° to 160° C. for about 0.5 to 10, preferably 1 to 7 hours.
• the halogenated polymer may then be reacted with sufficient unsaturated acid or anhydride at 100° to 250°usually about 180° to 220° C. for about 0.5 to 10, e.g., 3 to 8 hours. Processes of this general type are taught in U.S. Pat. Nos. 3,087,436; 3,172,892; 3,272,746 and others.
• the olefin polymer, and the unsaturated acid material are mixed and heated while adding chlorine to the hot material.
• Processes of this type are disclosed in U.S. Pat. Nos. 3,215,707; 3,231,587; 3,912,764; 4,110,349; 4,234,435; and in U.K. Pat. No. 1,440,219.
• halogen By the use of halogen, about 65 to 95 weight percent of the polyolefin will normally react with the dicarboxylic acid material. Thermal reactions, those carried out without the use of halogen or a catalyst, cause only about 50 to 75 weight percent of the polyisobutylene to react. Chlorination obviously helps to increase the reactivity.
• the dicarboxylic acid producing materials can also be further reacted with amines, alcohols, including polyols, amino-alcohols, etc., to form other useful dispersant additives.
• amines e.g., amines, alcohols, including polyols, amino-alcohols, etc.
• the acid producing material is to be further reacted, e.g., neutralized, then generally a major proportion of at least 50 percent of the acid units up to all the acid units will be reacted.
• Useful amine compounds for reaction with the hydrocarbyl substituted dicarboxylic acid material include mono- and polyamines of about 2 to 60, e.g., 3 to 20, total carbon atoms and about 1 to 12, e.g., 2 to 8, nitrogen atoms in a molecule. These amines may be hydrocarbyl amines or may be hydrocarbyl amines including other groups, e.g., hydroxy groups, alkoxy groups, amide groups, nitriles, imidazoline groups, and the like. Hydroxy amines with 1 to 6 hydroxy groups, preferably 1 to 3 hydroxy groups are particularly useful.
• Preferred amines are aliphatic saturated amines, including those of the general formulas: ##STR1## wherein R, R' and R" are independently selected from the group consisting of hydrogen; C 1 to C 25 straight or branched chain alkyl radicals; C 1 to C 12 alkoxy C 2 to C 6 alkylene radicals; C 2 to C 12 alkylamino C 2 to C 6 alkylene radicals; each s can be the same or a different number of from 2 to 6, preferably 2 to 4; and t is a number of from 0 to 10, preferably 2 to 7. At least one of R, R' or R" must be a hydrogen.
• Non-limiting examples of suitable amine compounds include: 1,2-diaminoethane; 1,3-diaminopropane; 1,4-diaminobutane; 1,6-diaminohexane; polyethylene amines such as diethylene triamine; triethylene tetramine; tetraethylene pentamine; polypropylene amines such as 1,2-propylene diamine; di-(1,2-propylene) triamine; di-(1,3-propylene)-triamine; N,N-dimethyl-1,3diamino-propane; N,N-di-(2-aminoethyl) ethylene diamine; N,N-di(2-hydroxyethyl)-1,3-propylene diamine; 3-dodecyloxypropylamine; N-dodecyl-1,3-propane diamine; tris hydroxymethylaminomethane (THAM); diisopropanol amine; diethanol
• amine compounds include: alicyclic cyclic diamines such as 1,4-di-(aminomethyl) cyclohexane, and heterocyclic nitrogen compounds such as imidazolines, and N-aminoalkyl piperazines of the general formula: ##STR2## wherein p 1 and p 2 are the same or different and are each integers of from 1 to 4, and n 1 , n 2 different and are each integers of from 1 to 3.
• Non-limiting examples of such amines include 2-pentadecyl imidazoline; N-(2-aminoethyl) piperazine; etc.
• one process for preparing alkylene amines involves the reaction of an alkylene dihalide (such as ethylene dichloride or propylene dichloride) with ammonia, which results in a complex mixture of alkylene amines wherein pairs of nitrogens are joined by alkylene groups, forming such compounds as diethylene triamine, triethylenetetramine, tetraethylene pentamine and corresponding piperazines.
• alkylene dihalide such as ethylene dichloride or propylene dichloride
• ammonia such as ethylene dichloride or propylene dichloride
• ammonia such as ethylene triamine, triethylenetetramine, tetraethylene pentamine and corresponding piperazines.
• Low cost poly ethyleneamine compounds averaging about 5 to 7 nitrogen atoms per molecular are available commercially under trade names such a "Polyamine H,” “Polyamine 400,” “Dow Polyamine E-100,” etc.
• Useful amines also include polyoxyalkylene polyamines such as those of the formulae: ##STR3## where "m” has a value of about 3 to 70 and preferably 10 to 35; and ##STR4## where "n” has a value of about 1 to 40 with the provision that the sum of all the n's is from about 3 to about 70 and preferably from about 6 to about 35 and R is a saturated hydrocarbon radical of up to ten carbon atoms, wherein the number of substituents on the R group is from 3 to 6.
• the alkylene groups in either formula (i) and (ii) may be straight or branched chains containing about 2 to 7, and preferably about 2 to 4 carbon atoms.
• the polyoxyalkylene polyamines above may have average molecular weights ranging from about 200 to about 4,000 and preferably from about 400 to about 2,000.
• the preferred polyoxylakylene polyamines include the polyoxyethylene and polyoxypropylene diamines and the polyoxypropylene triamines having average molecular weights ranging from about 200 to 2,000.
• the polyoxyalkylene polyamines are commercially available and may be obtained, for examples, from the Jefferson Chemical Company, Inc. under the trade name "Jeffamines D-230, D-400, D-1000, D-2000, T-403 ,” etc.
• the amine is readily reacted with the dicarboxylic acid material, e.g., alkenyl succinicanyhydride, by heating an oil solution containing 5 to 95 weight percent of dicarboxylic acid material to about 100 to 250° C., preferably 125° to 175° C., generally for 1 to 10, e.g.,2 to 6 hours, until the desired amount of water is removed.
• the heating is preferably carried out to favor formation of imides or mixtures of iraides and amides, rather than amides and salts. Reaction ratios can vary considerably, depending upon the reactants, amounts of excess amine, type of bonds formed, etc.
• amine e.g., bis-primary amine
• the dicarboxylic acid moiety content e.g., grafted maleic anhydride content.
• amine e.g., bis-primary amine
• one mole of olefin reacted with sufficient maleic anhydride to add 1.10 mole of maleic anhydride groups per mole of olefin when converted to a mixture of amides and imides about 0.55 moles of amine with two primary groups would preferably be used, i.e., 0.50 mole of amine per mole of dicarboxylic acid moiety.
• the nitrogen containing dispersant can be further treated by boration as generally taught in U.S. Pat. Nos. 3,087,936 and 3,254,025 (the entirety of which is incorporated by reference).
• THAN tris (hydroxymethyl) amino methane
• the tris (hydroxymethyl) amino methane (THAN) can be reacted with the aforesaid acid material to form amides, imides or ester type additives as taught by U.K. Pat. No. 984,409, or to form oxazoline compounds and borated oxazoline compounds as described, for example, in U.S. Pat. Nos. 4,102,798, 4,116,876 and 4,113,639.
• the ashless dispersants may also be esters derived from the long chain hydrocarbyl substituted dicarboxylic acid material and from hydroxy compounds such as monohydric and polyhydric alcohols or aromatic compounds such as phenols and naphthols, etc.
• the polyhydric alcohols are the most preferred hydroxy compound and preferably contain from 2 to about 10 hydroxy radicals, for example, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, and other alkylene glycols in which the alkylene radical contains from 2 to about 8 carbon atoms.
• polyhydric alcohols include glycerol, mono-oleate of glycerol, monostearate of glycerol, monomethyl ether of glycerol, pentaerythritol, dipentaerythritol, ere.
• the ester dispersant may also be derived from unsaturated alcohols such as allyl alcohol, cinnamyl alcohol, propargyl alcohol, 1-cyclohexane-3-ol, and oleyl alcohol.
• unsaturated alcohols such as allyl alcohol, cinnamyl alcohol, propargyl alcohol, 1-cyclohexane-3-ol, and oleyl alcohol.
• Still other classes of the alcohols capable of yielding the esters of this invention comprise the ether-alcohols and amino-alcohols including, for example, the oxy-alkylene, oxy-arylene-, amino-alkylene-, and amino-arylene-substituted alcohols having one or more oxy-alkylene, amino-alkylene or amino-arylene or amino-arylene oxy-arylene radicals.
• the ester dispersant may be di-esters of succinic acids or acidic esters, i.e., partially esterilied succinic acids; as well as partially esterified polyhydric alcohols or phenols, i.e., esters having free alcohols or phenolic hydroxyl radicals. Mixtures of the above illustrated esters likewise are contemplated within the scope of this invention.
• the ester dispersant may be prepared by one of several known methods as illustrated for example in U.S. Pat. No. 3,381,022.
• Mannich base type dispersants such as those described in U.S. Pat. Nos. 3,649,229 and 3,798,165 (the disclosures of which are hereby incorporated by reference in their entirety) may also be used in these compositions.
• Such Mannich base disperants can be formed by reacting a high molecular weight, hydrocarbyl-substituted mono- or polyhydroxy benzene (e.g., having a number average molecular weight of 1,000 or greater) with amines (e.g., polyalkyl polyamines, polyalkenyl polyamines, aromatic amines, carboxylic acid-substituted polyamines and the succinimide formed from any one of these with an olefinic succinic acid or anhydride) and carbonyl compounds (e.g., formaldehyde or para formaldehyde).
• Most such high molecular weight dispersants e.g., molecular weight greater than 2,000, may receive the enhanced stability to phase separation in "
• a very suitable diapersant is one derived from polyisobutylene substituted with succinic anhydride groups and reacted with polyethylene areinca, e.g., tetraethylene pentamine, pentaethylene hexamine, polyoxyethylene and polyoxypropylene areinca, e.g., polyoxypropylene aliamine, trismethylolaminomethane and pentaerythritol, and combinations thereof.
• One preferred diapersant combination involves a combination of (A) polyisobutene substituted with succinic anhydride groups and reacted with (B) a hydroxy compound, e.g., pentaerythritol, (C) a polyoxyalkylene polyamine, e.g., polyoxypropylene diamine, and (D) a polyalkylene polyamine, e.g., polyethylene diamine and tetraethylene pentamine using about 0.3 to about 2 moles each of (B) and (D) and about 0.3 to about 2 moles of (C) per mole of (A) as described in U.S. Pat. No. 3,804,763.
• A polyisobutene substituted with succinic anhydride groups and reacted with (B) a hydroxy compound, e.g., pentaerythritol
• C a polyoxyalkylene polyamine, e.g., polyoxypropylene diamine
• D a polyal
• Another preferred dispersant combination involves the combination of (A) polyisobutenyl succinic anhydride with (B) a polyalkylene polyamine, e.g., tetraethylene pentamine, and (C) a polyhydric alcohol or polyhydroxy-substituted aliphatic primary amine, e.g., pentaerythritol or trismethylolaminomethane as described in U.S. Pat. No. 3,632,511.
• Metal-containing rust inhibitors and/or detergents are frequently used with ashless dispersants.
• Such detergents and rust inhibitors include oil soluble mono-and di-carboxylic acids, the metal salts of sulfonic acids, alkyl phenols, sulfurized alkyl phenols, alkyl salicylates and napthenates.
• these metal-containing rust inhibitors and detergents are used in lubricating oil in amounts of about 0.01 to 10, e.g., 0.1 to 5, weight percent, based on the weight of the total lubricating composition.
• Highly basic alkaline earth metal sulfonates are frequently used as detergents. They are usually produced by heating a mixture comprising an oil-soluble sulfonate or alkaryl sulfonic acid, with an excess of alkaline earth metal compound above that required for complete neutralization of any sulfonic acid present and thereafter forming a dispersed carbonate complex by reacting the excess metal with carbon dioxide to provide the desired overbasing.
• the sulfonic acids are typically obtained by the sulfonation of alkyl substituted aromatic hydrocarbons such as those obtained from the fractionation of petroleum by distillation and/or extraction or by the alkylation of aromatic hydrocarbons as for example those obtained by alkylating benzene, toluene, xylene, napthalene, diphenyl and the halogen derivatives such as chlorobenzene, chlorotoluene and chloronaphthalene.
• the alkylation may be carried out in the presence of a catalyst with alkylating agents having from about 3 to more than 30 carbon atoms.
• alkaryl sulfonates usually contain from about 9 to about 70 or more carbon atoms, preferably from about 16 to about 50 carbon atoms per alkyl substituted aromatic moiety.
• the alkaline earth metal compounds which may be used in neutralizing these alkaryl sulfonic acids to provide the sulfonates includes the oxides and hydroxides, alkoxides, carbonates, carboxylate, sulfide, hydrosulfide, nitrate, borates and ethers of magnesium, calcium, strontium and barium. Examples are calcium oxide, calcium hydroxide, magnesium oxide, magnesium acetate and magnesium borate. As noted, the alkaline earth metal compound is used in excess of that required to complete neutralization of the alkaryl sulfonic acids. Generally, the amount ranges from about 100 to 220 percent, although it is preferred to use at least 125 percent of the stoichiometric amount of metal required for complete neutralization.
• a preferred alkaline earth sulfonate additive is magnesium alkyl aromatic sulfonate having a high total base number ("TBN") ranging from about 300 to about 400 with the magnesium sulfonate content ranging from about 25 to about 32 weight percent, based upon the total weight of the additive system dispersed in mineral lubricating oil.
• TBN total base number
• Neutral metal sulfonates are frequently used as rust inhibitors.
• Polyvalent metal alkyl salicylate and naphthenate materials are known additives for lubricating oil compositions to improve their high temperature performance and to counteract deposition of carbonaceous matter on pistons (U.S. Pat. No. 2,744,069).
• An increase in reserve basicity of the polyvalent metal alkyl salicylates and napthenates can be realized by utilizing alkaline earth metal, e.g., calcium, salts of mixtures of C 8 -C 26 alkyl salicylates and phenates (see '069) or polyvalent metal salts of alkyl salicylic acids, said acids obtained from the alkylation of phenols followed by phenation, carboxylation and hydrolysis (U.S. Pat. No. 3,704,315) which could then be converted into highly basic salts by techniques generally known and used for such conversion.
• the reserve basicity of these metal-containing rust inhibitors is usefully at TBN levels of between 60 and 150.
• polyvalent metal salicylate and naphthenate materials include the methylene and sulfur bridged materials which are readily derived from alkyl substituted salicylic or naphthenic acids or mixtures of either of both with alkyl substituted phenols.
• Basic sulfurized salicylates and a method for their preparation is shown in U.S. Pat. No. 3,595,791.
• Such materials include alkaline earth metal, particularly magnesium, calcium, strontium and barium salts of aromatic acids having the general formula:
• Ar is an aryl radical of 1 to 6 rings
• R 1 is an alkyl group having from about 8 to 50 carbon atoms, preferably 12 to 30 carbon atoms (optimally about 12)
• X is a sulfur (--S--) or methylene (--CH 2 --) bridge
• y is a number from 0 to 4
• n is a number from 0 to 4.
• overbased methylene bridged salicylate-phenate salt is readily carried out by conventional techniques such as by alkylation of a phenol followed by phenation, carboxylation, hydrolysis, methylene bridging a coupling agent such as an alkylene dihalide followed by salt formation concurrent with carbonation.
• An overbased calcium salt of a methylene bridged phenol-salicylic acid of the general formula: ##STR5## with a TBN of 60 to 150 is highly useful in this invention.
• the individual R groups may each contain from 5 to 40, preferably 8 to 20, carbon atoms.
• the metal salt is prepared by reacting an alkyl phenol sulfide with a sufficient quantity of metal containing material to impart the desired alkalinity to the sulfurized metal phenate.
• the sulfurized alkyl phenols which are useful generally contain from about 2 to about 14 percent by weight, preferably about 4 to about 12 weight percent sulfur based on the weight of sulfurized alkyl phenol.
• the sulfurized alkyl phenol may be converted by reaction with a metal containing material including oxides, hydroxides and complexes in an amount sufficient to neutralize said phenol and, if desired, to overbase the product to a desired alkalinity by procedures well known in the art.
• a metal containing material including oxides, hydroxides and complexes in an amount sufficient to neutralize said phenol and, if desired, to overbase the product to a desired alkalinity by procedures well known in the art.
• Preferred is a process of neutralization utilizing a solution of metal in a glycol ether.
• the neutral or normal sulfurized metal phenates are those in which the ratio of metal to phenol nucleus is about 1:2.
• the "overbased” or “basic” sulfurized metal phenates are sulfurized metal phenates wherein the ratio of metal to phenol is greater than that of stoichiometric, e.g., basic sulfurized metal dodecyl phenate has a metal content up to (or greater) than 100 percent in excess of the metal present in the corresponding normal sulfurized metal phenates. The excess metal is produced in oil-soluble or dispersible form (as by reaction with CO 2 ).
• Dihydrocarbyl dithiophosphate metal salts are frequently added to lubricating oil compositions as antiwear agents. They also provide antioxidant activity.
• the zinc salts are most commonly used in lubricating oil in amounts of 0.1 to 10, preferably 0.2 to 2 weight percent, based upon the total weight of the lubricating oil composition. They may be prepared in accordance with known techniques by first forming a dithiophosphoric acid, usually by reaction of an alcohol or a phenol with P 2 S 5 and then neutralizing the dithiophosphoric acid with a suitable zinc compound.
• Mixtures of alcohols may be used including mixtures of primary and secondary alcohols, secondary generally for importing improved antiwear properties, with primary giving improved thermal stability properties. Mixtures of the two are particularly useful.
• any basic or neutral zinc compound could be used but the oxides, hydroxides and carbonates are most generally employed.
• Commercial additives frequently contain an excess of zinc due to use of an excess of the basic zinc compound in the neutralization reaction.
• the zinc dihydrocarbyl dithiophosphates useful in the present invention are oil soluble salts of dihydrocarbyl esters of dithiophosphoric acids and may be represented by the following formula: ##STR7## wherein R and R' may be the same or different hydrocarbyl radicals containing from 1 to 18, preferably 2 to 12 carbon atoms and including radicals such as alkyl, alkenyl, arylaralkyl, alkaryl and cycloaliphatic radicals. Particularly preferred as R and R' groups are alkyl groups of 2 to 8 carbon atoms.
• the radicals may, for example, be ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec- butyl, amyl, n-hexyl, i-hexyl, n-octyl, decyl, dodecyl, octadecyl, 2-ethylhexyl, phenyl, butyl-phenyl, cyclohexyl, methylcyclopentyl, propenyl, butenyl, etc.
• the total number of carbon atoms (i.e., R and R') in the dithiophosphoric acid generally should be about 5 or greater.
• a material which has been used as an antioxidant in lubricating oil compositions containing a zinc dihydrocarbyl dithiophosphate and ashless dispersant is copper, in the form of a synthetic or natural carboxylic acid salt.
• examples include C 10 to C 18 fatty acids such as stearic or palmitic acid.
• unsaturated acids such as oleic acid
• branched carboxylic acids such as naphthenic acids
• synthetic carboxylic acids are all used because of the acceptable handling and solubility properties of the resulting copper carboxylates.
• Suitable oil soluble dithiocarbamates have the general formula (RR' N C SS) n Cu; where n is 1,2 and R and R' may be the same or different hydrocarbyl radicals containing from 1 to 18 carbon atoms and including radicals such as alkyl, alkenyl, aryl, aralkyl, alkaryl and cycloaliphatic radicals. Particularly preferred as R and R' groups are alkyl groups of 2 to 8 carbon atoms.
• the radicals may, for example, be ethyl, n-propyl, n-butyl, i-butyl, sec-butyl, amyl, n-hexyl, i-hexyl n-octyl, decyl, dodecyl, octadecyl, 2-ethylhexyl, phenyl butyl-phenyl, cyclohexyl, methylcyclopentyl, propenyl, butenyl, etc.
• the total number of carbon atoms i.e., R and R'
• R and R' generally should be about 5 or greater.
• Copper sulfonates, phenates and acetyl acetonates can also be used.
• antioxidants are used in amounts such that, in the final lubricating or fuel composition, a copper concentration of from about 5 to about 500 ppm is present.
• hydrocarbyl succinic acid metal salts used in this invention may be used in place of at least a portion of these antioxidants.
• the metal salts suitable for use in this invention include those materials having metals from Groups 1b, 2b, 3b, 4b, 5b, 6b, 7b and 8 of the Periodic Table (e.g., Li, Na, K, Rb, Cs, Mg, Ca, Sr, 8a, Cu, Cd, Zn). Preferred are metals from Groups 1b and 2b. Most preferred is copper, whether in the cuprous or cupric ion form, and zinc.
• the salts themselves may be basic, neutral or acidic. They may be formed by reacting (a) any of the materials discussed above in the Diapersant section, which have at least one free carboxylic acid group with (b) a reactive metal compound. Suitable reactive metal corn pounds include those such as cuptic or cuprous hydroxides, oxides, acetates, borates, and carbonates, basic copper carbonate or the corresponding zinc compounds.
• Examples of the metal salts of this invention are Cu and Zn salts of polyisobutenyl succinic anhydride (hereinafter referred to as Cu-PIBSA and Zn-PIBSA, respectively), and Cu and Zn salts of polyisobutenyl succinic acid.
• the selected metal employed is its divalent form, e.g., Cu +2 .
• the preferred substrates are polyalkenyl succinic acids in which the alkenyl group has a molecular weight greater than about 700.
• the alkenyl group desirably has a M n from about 900 to 1400, and up to 2500, with a M n of about 950 being most preferred.
• PIBSA polyisobutylene succinic acid
• a solvent such as a mineral oil
• a water solution or slurry
• Heating may take place between 70° and about 200° C.
• Temperatures of 110° to 140° C. are entirely adequate. It may be necessary, depending upon the salt produced, not to allow the reaction mixture to remain at a temperature above about 140° C. for an extended period of time, e.g., longer than 5 hours, or decomposition of the salt may occur.
• the metal salts of this invention (e.g., Cu-PIBSA, Zn-PIBSA, or mixtures thereof) will be generally employed in an amount of from about 1-1,000 ppm by weight of the metal, and preferably from about 50-500 ppm by weight of the metal, in the final lubricating or fuel composition.
• a polyisobutenyl succinic anhydride (PIBSA) was prepared from a polyisobutylene (PIB) molecule of 1,300 M n by heating a mixture of 100 parts of polyisobutylene with 13.5 parts of maleic anhydride to a temperature of about 220° C. When the temperature reached 120° C., the chlorine addition was begun and 8.3 parts of chlorine at a constant rate was added to the hot mixture for about 5.5 hours. The reaction mixture was then heat soaked at 220° C. for about 1.5 hours and then stripped with nitrogen for about one hour.
• PIBSA polyisobutenyl succinic anhydride
• the PIBSA product was 83.8 weight percent active ingredient (a.i.), the remainder being primarily unreacted PIB.
• the product was then diluted with S 150 N to an ASTM Saponification Number of 69 and an a.i. of 59.
• Each concentrate blend contained about equal amounts of a PIBSA-polyamine dispersant, overbased magnesium sulfonate detergent, ZDDP, nonylphenol sulfide, and friction modifier together with the components listed below by weight %:
• Example 4 The concentrates of Example 4 were blended as described in that Example with the exception that the two blends contained the same copper oleate concentration and various levels of either PIBSA or Zn-PIBSA instead of the Cu-PIBSA.
• Example 3 provides better compatibility and stability than does the PIBSA alone and does so at a lower concentration.

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• 1987
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